3 Thought Experiments to Simplify Your Trip Planning

Travelers seem to fall into two categories: those who think planning a trip is almost as fun as being on the actual trip, and those who save getting organized until the last minute because it’s so insanely tedious.

Much as I’d like to be one of those trip-planning junkies, I’ve always fallen into the latter category. I love the results of my trip planning: I love scoring a guesthouse that seems far too awesome to be so cheap; I love knowing which local dishes to try and the best places to find them; and I love the excitement of seeing, in person, all the sites that I once only knew as distant photos online. For all the people who loathe trip planning as much as I do, here are my tips for keeping it simple, manageable, and minimally overwhelming.

Begin with the Big Picture

Whether you’re visiting one city or dozens on any given trip, I find that figuring out where to start can be the biggest challenge. Do I start with guesthouses so I know I have a place to stay? Or transportation so I know how to get to those guesthouses plus all the other places I want to see? Rather than sinking into a sea of details, I ease myself in slowly and start by figuring out the big picture. What is this country or city all about? Is it charming, friendly and beautiful? Or is it gritty, raw and challenging? Does it seem to be how imagined it? Do I even really want to go there?

For me, blogs are the best place to go for this basic information. It’s easy to get lost in all the information available online and in thousand-page guidebooks, but blogs break it down into the recent experiences of one or two people. It feels like a safe, uncomplicated, and informative base to build upon. I pick up a few initial tips, get to know this strange place I might visit a little better, and gradually start diving further into the research process, inch by inch.

Remember Why You Want to Go

I’ll admit that I’m kind of a suggestible person, and the more research I do, the more “must-see” places and attractions I keep adding to my list. If I read that a certain attraction is important, I suddenly feel like I have to go there.

I was reminded of the ridiculousness of my crazy need to see absolutely everything when some friends came to visit Brent and me when we were living in Japan. We were chatting about their trip to Nara, and I asked if they’d seen the enormous Buddha in Todai-ji Temple, since it’s one of the most famous sites in the city. They told me they’d seen a few temples, but they didn’t hear about the famous Buddha until after they left. “Oh no!” I gasped, imagining how horrified I’d be if I missed such a significant site. My friend shrugged, “I figure if I’d never heard of it before I came to Japan, it’s probably not a big deal that I missed it”.

It was an off-the-cuff comment, but it really put my approach to planning in perspective. Like most people, my reasons for wanting to visit a particular place are rarely about one particular monument, attraction or temple; it’s usually much bigger than that. I want to visit a place because I’ve heard wonderful things about the scenery, the architecture, the food, or the people. Now, when I find myself getting overwhelmed by all the “must-see” attractions, I go back and remember why I wanted to visit in the first place. It helps me separate the experiences and sites that really matter to me, from the ones that only became important after a guidebook told me so.

Don’t Ruin the Surprise

I’m always slightly envious when I meet travelers who fully admit to having come to a place without doing much planning or research in advance. They seem particularly amazed by everything they see and do, because they had no absolutely expectations. Instead, they arrive open, ready to learn from the people they meet along the way, and eager to discover the place by exploring it first-hand.

I think I’ll always be someone who needs to do at least some research beforehand, but there’s definitely something to be said for leaving a little to the imagination. Preparing to visit a new place is a bit like being a kid a few days before Christmas: It kind of ruins the fun if you peek underneath the wrapping paper, and find out exactly what you’re getting. I think you can suck some of the magic out of travel when you over-prepare and try to learn everything about a place before you even get there. It’s good to have some idea of what to expect, but it’s just as important to leave some things unknown, and leave room to be surprised.

How Do You Keep Your Trip Planning Simple?

13 thoughts on “3 Thought Experiments to Simplify Your Trip Planning”

  1. What a great post! I enjoyed reading it.

    I am definitely one of those who does little or no research and planning before a trip, though it’s not always because I’m aware of wanting to keep the surprise. Sometimes I’m just too busy or lazy. I do, however, always find a place to stay for at least the first couple nights before going somewhere, because not having a place already lined up is stressful for me. However, aside from that, I don’t really plan. I love just asking locals what they like, finding out other travellers favourite spots, and wandering on my own. I think it really opens one up to the the happy surprises and hidden gems that we can miss otherwise, rushing from one attraction to the next.
    (though I totally support “attraction” people – I know quite a few) Really, I think travel should be done in a way that makes you happy and allows you to enjoy, whatever that looks like for each individual. 🙂

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